Hydrogen Bromide → (S)-(+)-2-Amino-4-bromobutyric Acid Hydrobromide

HRID 2069173Notes

Reaction equation

HRID 2069173 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].[BrH:8]>CC(O)=O>[BrH:8].[NH2:1][C@@H:2]([CH2:6][CH2:5][Br:8])[C:3]([OH:4])=[O:7]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 445963L-Homoserine lactone

Product 1

HCID 2733672(S)-(+)-2-Amino-4-bromobutyric Acid HydrobromideYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(S)-3-aminodihydrofuran-2(3H)-one hudrochloride (10.30 g, 74.87 mmol) in 58 mL of 30% w/w HBr in HOAc was stirred at 65° C. for 30 hrs. The solvent was removed under reduced pressure and the resulted solid was suspended in MTBE (200 mL) and stirred for 30 min. The solid was collected by filtration and washed with MTBE (200 mL) and dried to give (S)-2-amino-4-bromobutanoic acid hydrobromide as white solid (19.33 g, 98%). 1H NMR (400 MHz, d6-DMSO) δ 8.37 (s, 3H), 4.01 (m, 1H), 3.65 (m, 2H), 2.33 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe solid was collected by filtration
  3. washwashed with MTBE (200 mL)
  4. customdried

Sources & evidence

ORD record
ord-8d1d6032ea494fb1b7952270ba46c5f5
Source dataset
uspto-grants-2012_10
Patent number
US08299021B2

Reaction notes

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